


Eleven Glasses of Whiskey

by thepopeisdope



Series: 12 Days of Christmas [11]
Category: Supernatural
Genre: Bartender Dean, Christmas Fluff, M/M
Language: English
Status: Completed
Published: 2015-12-24
Updated: 2015-12-24
Packaged: 2018-05-09 11:50:15
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,988
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5538779
Author URL: https://archiveofourown.org/users/thepopeisdope/pseuds/thepopeisdope
Summary: <blockquote class="userstuff">
              <p>A guy in a trench coat walks into a bar, and no, it isn't the start of a bad joke.</p>
            </blockquote>





	Eleven Glasses of Whiskey

**Author's Note:**

> So... Let's all pretend this was posted on the 24th, yeah? Cool. Shout out to AO3 for giving me the option to make it look like I'm not a total failure.
> 
> Day 12 will hopefully be up tomorrow, day after at the latest.

Trench coat guy comes in about halfway through Dean’s shift. He doesn’t make a scene when he pushes through the Roadhouse’s front door, like so many people are bound to do when they’re having a shitty day. And this guy? Definitely having a shitty day. Every fiber of his being screams it.

Dean watches him as he makes his way to one of the many empty seats at the bar, very obviously avoiding the other patrons every step of the way. The guy’s eyes are downcast, his shoulders hunched. His eyes are red-rimmed.

Bad signs, all of them. And on Christmas Eve, no less.

Dean sighs. He hasn’t even spoken to the guy yet, and already his heart aches for him and whatever hardships he’s facing that have him so down.

Okay, so maybe Dean’s concerning himself a bit much over a complete stranger. But the holidays are about being good people, right? If anyone in the Roadhouse needs some kindness right now, it’s this random-ass guy in his rumpled trench coat.

Dean casts a glance over his shoulder at Jo, and is relieved to find her chatting with a customer at the opposite end of the bar. A chatty Jo is a distracted Jo, and Dean does _not_ need every detail of this being relayed to Sam down the grapevine. Anything Jo knows, Sam is sure to also know within an hour.

Married couples are annoying like that.

Dean had been absently wiping out a glass with a towel when Mr. Trench Coat walked in, but now he puts the glass down, slings the towel over his shoulder, and heads toward the guy’s chosen seat. He puts on his most charming smile—which is definitely not a struggle, given how damn _hot_ the guy is—and greets, “Hey, welcome to the Roadhouse. Anything I can get you?”

The guy startles slightly, like he somehow hadn’t noticed Dean’s approach and subsequent leaning against the opposite side of the bar. He then proceeds to stare at Dean for a good thirty seconds, which in and of itself is a whole new level of amusing, before clearing his throat and replying, “I’ll have a whiskey, please. Neat.”

The deep roughness of the guy’s voice takes Dean by surprise, but he deals with more than enough surprising people in his line of work to be able to make it well. That being said, he adds _nice to listen to_ and _polite as hell_ to his list of the guy’s positive traits, right under _crazy blue eyes_ and _great jawline_.

And _whoa_ , when the hell did Dean’s brain decide a _list_ was a good idea?

Dean forces his way out of his thoughts and nods in response to Mr. Trench Coat’s order, then turns to grab a bottle of whiskey from the shelf behind him. And if he automatically reaches for the top-shelf stuff… Well. Attractive or otherwise, this guy looks like he needs it. Just like he also needs a generous pour, and Dean’s declaration of “On the house,” when he slides the glass over.

The guy’s eyes widen. Dean sees them flick toward the label on the bottle, no doubt recognizing the value he is getting. “Why?”

From the other side of the bar, Jo calls Dean’s name, effectively ending his chance to chat—flirt?—with trench coat guy. With the few seconds he has, Dean shoots the guy a wink and says simply, “Merry Christmas.”

The guy looks too baffled to respond, but his cheeks take on a faint reddish tint. Dean grins at the sight, then turns on his heel to go find out what Jo needs.

Dean only just catches the faint reply the guy directs toward him. “Merry Christmas.”

~

Unfortunately, Dean doesn’t get a chance to revisit trench coat guy over the next couple of hours. Jo sends him to the back to do a round of dishes (and he doesn’t have much of a choice, given they’re the only two employees manning the Roadhouse tonight), and after that, the bar is kept busy by a moderately-large group of women who come from god-knows-where and order round after round of peppermint martinis. It’s obnoxious, and far more work than a Christmas Eve shift typically entails, but at least the tips are good.

Once the women finally leave, Dean and Jo are both feeling exhausted, and the clock is nearing midnight. They aren’t set to close for another hour and a half, which Jo loudly bemoans.

“I just want to _sleep_ ,” she says, leaning her forehead into Dean’s chest. “What if we just close now instead?”

Dean takes a glance around the bar, assessing the customers still left. He sees two of their regulars on one side of the bar, each sipping absently at their drinks in their usual styles, and on the other side…

Trench coat guy, nursing a glass of whiskey and looking for all the world like a lost puppy. If it were just the regulars left, Dean might have agreed to closing up early. But with trench coat guy still here? Not going to happen.

Dean gently pushes Jo away from him and in the general direction of the back room, ruffling her hair as he does. “I can finish on my own tonight,” he says. “Go home and cuddle with your husband, or something equally gross.”

Jo instantly perks up, her exhaustion fading in the light of her excitement. “Dean, are you sure? You don’t mind?”

“We literally have three customers, Jo.” Dean rolls his eyes, nudges her a bit further. “I’ll be fine.”

Jo throws her arms around Dean in a tight hug, and now retreats toward the back room of her own volition. “Dean Winchester, I owe you so big for this one. Thank you.”

Dean scoffs, but he can’t help but grin. “ _Go_ , Joanna, before I change my mind. Say hi to Sam for me.”

“Will do!” Jo replies as she disappears through the door. “Merry Christmas, Dean!”

Dean doesn’t bother returning the sentiment, knowing that she won’t hear him anyway.

The bar is already extra quiet without Jo there, only some faint Christmas music from the stereo system preventing complete silence, but Dean doesn’t mind. It’s only himself and a few easy customers left, how bad could that be to manage? And he only has to do it for just over an hour.

The two regulars don’t seem to have even moved when Dean looks over to check on them, which, alright, is a _little_ weird. But they’re regulars for a reason, and if this is how they’re choosing to spend their Christmas Eve, Dean isn’t going to object.

Trench coat guy is staring at him. Or at least, he is until Dean glances over and catches him in the act, at which point he quickly drops his gaze to his glass of whiskey.

Well. There’s no time like the present.

Dean goes and resumes the position he had been in when talking to the guy previously, leaning on his elbows against the bar. He isn’t quite sure how to break the ice, so he goes for the most obvious conversation starter he can think of and asks, “That isn’t the same glass that I gave you, is it? Jo helped you out, I hope?”

The guy blinks up at him, and again, Dean gets the impression that he’s surprised he’s being spoken to. “Jo,” he repeats. “The blond woman?”

Dean smiles. “That’s the one. Is that a yes?”

He nods. “Yes, she… helped me out. This is my third glass, I believe.” His eyes search Dean’s face for a moment, and he continues, “I don’t believe I caught your name.”

Dean stands up a bit straighter against the bar and sticks out a hand. “Dean. And you are?”

The guy is slow to take Dean’s hand, but when he does, his grip is firm. “I’m Castiel.”

“ _Castiel_ ,” Dean repeats, just to get a feel of the name on his tongue. It’s interesting. Unusual, even, but it has a unique charm that seems to fit the man across from him. He likes it, but he still asks for convenience’s sake, “Mind if I call you Cas?”

Cas gives him a small smile. “That's fine. A lot of people do.”

“Alright, cool,” Dean says with a nod. “Well, Cas, since I’ve already bought you a drink, you mind if I ask what brought you in here tonight? Guy like you must have someone waiting for you at home, right?”

Cas blushes lightly and looks down at his glass again, contemplating the amber liquid within. “No, I uh… I don’t. Don’t have much of anyone anywhere at the moment.”

So he’s available. Fucking sweet.

But aside from that, there’s a quiet pain behind Cas’ words, and Dean winces in sympathy. He’s been there too, back before he got his job at the Roadhouse and finally figured himself out. He knows what it’s like. “Do you need to talk about it?” he offers, because knowing what it’s like, he also knows that every once in a while, you need to unload.

Cas slowly raises his eyes to Dean’s again, appraising him. A moment passes, and he sighs. “I quit my job,” he confesses. “My superiors were rude, abusive toward their subordinates, and just unpleasant to be around in general. My brother was always pushing me to leave, but it was good money, so I didn’t. It was pretty much the only job I ever had, and now that I’m out, I don’t have any idea what I’m going to do with myself.” He had picked up speed as he spoke, fueled by frustration that has clearly been building up for a while, and as soon as he's finished his entire body seems to deflate. “Sorry. I'm sure you don’t want to be listening to this right now.”

Dean smiles. “I think you’re really underestimating me, Cas. Besides—you’re not exactly keeping me from anything.” He glances pointedly over his shoulder. The two regulars are still in place, and thankfully neither are in need of a refill yet. Cas still looks hesitant to accept Dean’s answer, so Dean plows on with, “Congrats with getting out of a shitty job, then. Where did you work, what did you do?”

Cas takes a nervous drink of his whiskey, like his answer is something he’s ashamed to admit. “I think the easiest way to describe it is ‘personal security’, but it was probably even less conventional than that makes it sound. I… signed confidentiality agreements, so I probably shouldn’t talk about it in too much detail.”

Dean’s jaw drops. “Dude, are you serious? You were… what? A bouncer, thug? Hitman? Secret Service?”

The suggestions draw a chuckle out of Cas, though which one in particular he finds amusing is impossible to determine. It should probably be a bit concerning that each of them is plausible, but Cas is fucking hot as it is, and the idea of him in a uniform, maybe carrying a gun…

Dean chooses not to dwell on that image for too long. His weird kinks can be explored later, when he’s not at _work_ , of all places.

Cas, the prick, can obviously see just how thoroughly he has grabbed Dean’s attention, because he only smirks and says, “Something like that.” His smile is quick to fade, however. His eyes go distant, and his earlier sadness resurfaces in their blue depths. “I don’t know what I’m going to do, now. I have no job, no place to stay. I came to Lawrence to try to find my brother, but as far as I’ve been able to piece together, he’s in India with his girlfriend for the next few months.” He slams his head down onto the bar with a dull _thunk_.

Dean has a response for that ready on the tip of his tongue, but before gets the chance to put it to voice, one of the customers on the other side of the bar calls for him. He raps his knuckles against the polished surface of the counter and mutters to Cas, “Be right back,” then goes to help the other man.

All the man needs is to clear his tab, which Dean handles with practiced ease. He bids the man goodnight and a merry Christmas, but as Dean turns to head back to Cas—who’s head is still on the bar, amusingly enough—the last patron signals for him as well. He takes her payment just as quickly as he had the man’s, and within minutes, the bar is empty save for himself and Cas.

He has an idea. Just an inkling of one.

“Cas, you ever work in a bar?”

Cas finally lifts his head from the bar to peer suspiciously at Dean. “Why?”

Dean rolls his eyes, crossing his arms and propping his hip against the counter as he watches Cas. “Just answer the damn question, man.”

Cas narrows his eyes, but concedes. “I worked in a bar over the summer one year during college,” he says. “But my cousin Gadreel owned it, so my employment was hardly an accomplishment.”

“But you did work in a bar,” Dean reiterates. “And your last job was, essentially, hired muscle.”

“Something like that,” Cas says, an echo of his previous statement on the matter that makes Dean smile. “But I don’t understand why you’re asking me this.”

“ _Because_ , dumbass, I’m about to offer you a job.”

Cas blinks. “You… what? Why would you do that?”

Dean shrugs. “Because you don’t have a job, you need a job, I can _get_ you a job, and I’m just that fantastic of a guy.” He ticks off each of his points on his fingers as he goes, then brandishes the raised digits as if that will further cement his argument. “So do you want the job or not?”

“Dean, I… I don’t know what to say.” Cas clutches at the nearly-empty glass of whiskey in front of him like a lifeline, looking frazzled. “Are you truly willing to hire me? Are you the owner?”

“I’m the manager,” Dean corrects, “but that’s still enough to give me power over new hires. Plus, the owner is my sister-in-law’s mother. I’m pretty sure we can convince her you’re cool. She always talks about wanting some extra muscle to help with the riffraff, too, so that’s another point in your favor.”

Cas seems to be getting excited now, but he is also clearly trying not to get his hopes up too high. “I’ll probably have to meet the owner first, right? Could you… arrange for me to meet with her? I can do a formal interview, if you’d like. Print a copy of my resume.”

“Or…” Dean starts hesitantly, “if you want, you could just have a casual chat with her? Maybe like… tomorrow.”

Cas opens his mouth like he is about to agree, but snaps it shut again as he thinks it over. “Tomorrow is Christmas,” he states, and _yeah_ , Dean knows. “I wouldn’t want to disturb her on Christmas. My need for a job isn’t _that_ dire.”

“No, yeah, I know,” Dean says quickly, stumbling over his words. This is something he _wants_ to ask, but he doesn’t know if he _should_.

One look at Cas’ wide, blue eyes has him taking the risk. He’s always been a sucker for blue eyes.

“See, we’re having dinner tomorrow, at my brother and Jo’s house,” Dean explains. “Ellen will be there, of course, and a bunch of our other friends and family. So I was thinking maybe you’d want to go with me? Jo’s been harassing me about finding a _plus one_ for weeks now, and since your brother’s out of town and you’re alone as it is—”

“Dean,” Cas interrupts, “are you giving me a job _and_ asking me to be your date to a Christmas party?”

Dean swallows hard. “Uh… Yes? I probably shouldn’t do that, huh? Is that unprofessional? It’s unprofessional. You don’t have to accept, don’t worry.”

Cas grins and shakes his head. “It’s not a problem, Dean,” he promises. “In fact, it might be for the best. This way I know I won’t be starting a new job with an awkward, unrequited crush on a coworker.”

Dean has to laugh at that. “Yeah, well maybe you can save me from that same boat, alright? Is that your version of a yes?”

Cas laughs, too. “Yes, Dean, I would love to accompany you to your brother’s party tomorrow.”

“Great.” Dean leans further over the bar and into Cas’ space, fishing his phone out of his pocket and handing it to the other man as he does. “I think I’m going to need your number, too. For… y’know. Professional reasons.”

Cas takes the offered cell phone and punches in his information. He hands it back with a smirk. “And maybe for less than professional reasons too, I hope.”

“Oh, absolutely.”

~

Unsurprisingly, Ellen loves Cas. (Actually, _everyone_ loves Cas, but that’s beside the point.) He passes every one of the tests she gives him, and when the time comes in the evening that he even manages to outdrink her, she offers him a job on the spot. Cas grins and thanks her half a dozen times, and after shaking her hand to seal the deal, he throws his arms around Dean in a hug.

Dean might intentionally make sure they ‘find’ themselves under the mistletoe after that, but since it gets no complaints from Cas—as far opposite as you could get, actually—Dean refuses to listen to Sam’s half-hearted reprimandings for his behavior.

Okay, so maybe Dean and Cas make a _slight_ spectacle during the supposed ‘family dinner’, but so what? Their relationship is new and exciting to them both, and if figuring out how they fit together means getting bitched at by Sam, so be it.

They fit together pretty damn well, Dean thinks.

**Author's Note:**

> Follow me on [tumblr](http://thursdays-fallen-angel.tumblr.com/)!


End file.
